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Large‐Scale Enantiomeric Enrichment via Solid State Extraction Using β‐Cyclodextrin Crystalline and Anhydrous Acetonitrile as Solid and Liquid Phases
Author(s) -
Chen Shushi
Publication year - 1997
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199700097
Subject(s) - chemistry , anhydrous , acetonitrile , triethylamine , enantiomer , chromatography , extraction (chemistry) , cyclodextrin , solid phase extraction , solvent , organic chemistry
The process‐scale enantiomeric enrichment of several adrenergic β‐blockers, atropine, and ruelene was accomplished through solid state extraction using anhydrous acetonitrile and β‐cyclodextrin crystalline as liquid and solid phases, respectively. This non‐chromatographic method has the advantages of easy, low cost operation, simplicity, and a high percentage of enrichment for some of the β‐blockers examined in a single batch. The percentage of enrichment in anhydrous acetonitrile was the best for all the racemates studied; however, it dropped dramatically when the extraction was carried out in a liquid phase of low polarity such as petroleum ether. No enantiomeric enrichment was observed in liquid phases that are polar and capable of participating in hydrogen bonding (e.g., methanol). Introducing additives (e.g., acetic acid, triethylamine) to the liquid phase also decreased the percentage of enrichment. Finally, lowering the operating temperature (0 °C) appeared to retard the enantiomeric extraction process, which could be restored to normal level by elevating liquid phase temperature to 28 °C.